Water → HCID 18476092, compound

HRID 2288705Notes

Reaction equation

HRID 2288705 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[CH:11][C:12]3[C:13]([CH:17]=2)=[N:14][O:15][N:16]=3)[C:5]([OH:8])=[CH:6][CH:7]=1.[C:18](=O)([O-])[O-].[K+].[K+].CI.O>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[CH:11][C:12]3[C:13]([CH:17]=2)=[N:14][O:15][N:16]=3)[C:5]([O:8][CH3:18])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 135592939HCID 135592939, compound

Product 1

HCID 18476092HCID 18476092, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
18 °C

Procedure

A stirred mixture of 5-(3-bromo-6-hydroxyphenyl)benzofurazan (8.70 g, 30 mmol), potassium carbonate (14.42 g, 90 mmol) and methyl iodide (2.83 mL, 45 mmol) in dimethylformamide (100 mL) is stirred at 18° C. for 16 h. The mixture is then treated with water (600 mL) and extracted with ethyl acetate (3×150 mL). The combined extracts are washed (saturated NaCl), dried (Na2SO4), filtered and the solvent is evaporated off under reduced pressure to yield the crude product which is purified by recrystallisation from t-butylmethyl ether-hexane to give 5-(3-bromo-6-methoxyphenyl)benzofurazan as a beige crystalline solid, m.p. 135-137° C.

Workup

  1. extractionextracted with ethyl acetate (3×150 mL)
  2. washThe combined extracts are washed (saturated NaCl)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvent is evaporated off under reduced pressure
  6. customto yield the crude product which
  7. customis purified by recrystallisation from t-butylmethyl ether-hexane

Sources & evidence

ORD record
ord-9b1fd93feea9499cabe78795cab59ce0
Source dataset
uspto-grants-2000_07
Patent number
US06090817

Reaction notes

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